Do you trust yourself?

To remember the little things? Prioritize the big things? Cope when your plans ignite?

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #37. ✨

Do you trust yourself?

Suspended over Squamish, captured on Kodak Portra 400 film

In the months after graduation, my friend Carolyn and I Gchatted covertly from the cubicle farms of our respective first jobs, commiserating over the mild indignities of post-collegiate life.

“How are people with desk jobs and commutes balancing all of these adult responsibilities,” we’d type back and forth in wonderment. “Like, the people that do their laundry and grocery shop on the same night after work. Genuinely, how do they do it?!”

To be fair, Amazon Fresh was still a gleam in Jeff Bezos’ eye, and neither of us had snagged the renter’s holy grail of in-unit laundry. (My own building’s washing machines were perennially out of service, so laundry night found me dragging pillowcases full of dirty clothing to a laundromat whose dryers scorched my bedsheets.) And yet…!

I look back on those days with a bit of embarrassment, but a lot of empathy for the overgrown kids we were. We had no clue what we were in for.

At some point, I downloaded a reminder app to keep my accumulating adult responsibilities straight.

Those responsibilities had grown more complex than the laundry-and-grocery-shopping days of yore—and more numerous, judging by the constant pinging of my phone. Figure out how to sell Mom’s car if we can’t find the title. Confirm which health insurance plans are contracted with my doctors.

Sometimes, this reminder app feels like a very thin membrane separating my mostly-functional existence from encroaching entropy.

This week, I did a walkthrough of my house with a plumber; he mentioned that homeowners should recaulk their showers and tubs every three to five years.

Instinctively, I pulled out my phone to record this task in my reminder app. January 2027, I tapped with my thumbs. Recaulk bathrooms!!!

No sooner had I punched in the reminder than I experienced what I can only describe as existential backdraft. I’m a responsible person, I thought. When did I stop trusting myself to remember this kind of thing?

But, of course, this was about more than remembering tasks or logistical details.

My time-blocking habit used to be a lifesaver at work—helping me manage deadlines, indicating when I’d overcommitted myself—but at some point, I started applying the tactic to my off-hours, too.

I’ve been a runner for more than twenty years. Do I really need to time-block a workout into my day, or set a reminder urging me to lace up my Sauconys? Haven’t I gathered enough evidence to assure myself that I’ll just…make it happen?

When did I stop trusting myself to do the things that are important to me?

Maybe you can relate to my reliance on reminder apps and time-blocking. Perhaps your particular brand of coping with adulthood’s onslaught of responsibility looks different.

Either way, you may have noticed the slippery slope between “building systems to manage modern life” and “over-structuring as a futile attempt at staving off uncertainty.” Specifically, the dark side of uncertainty: those smaller problems that threaten to upend our days, and the bigger ones that threaten to upend everything we’ve worked for.

Two weeks ago, I noticed a small issue in my shower, so I called the aforementioned plumber. Cut to today: tile has been stripped from the walls, the tub is sitting in my backyard, and I have a friendly insurance claims adjuster on speed-dial. (Hi, Dan!)

Fortunately and unfortunately, it’s a turn of events unrelated to anything I did (or didn’t do) as a homeowner. I say fortunately because this knowledge helps me avoid berating myself as I navigate the unwelcome, new-to-me world of water mitigation experts and general contractors eager for my emergency bathroom renovation business. I say unfortunately because it’s a reminder that I can do everything right and bad things will happen anyway.

After all, it is magical thinking to believe that we can prevent the invasive, sometimes painful onslaught of uncertain events.

When I was newly separated, my boss started discussing—glowingly and unprompted—the power of couples’ therapy. How healthy it kept her relationship! After the third mention, I began wondering whether she suffered from innocent tone-deafness or mild sociopathy.

And each time, I held my tongue instead of saying what I knew to be true: couples’ therapy is wonderful. It’s also not a divorce vaccine.

Today, I look back on these episodes with less irritation and more compassion. Self-satisfaction about “doing relationships right” serves as a coping mechanism, a pretense that we can keep a mutable human connection within our locus of control.

We adopt magical thinking and coping mechanisms because, on some level, we’re worried we can’t endure the worst what-ifs.

Sometimes, when I asked my financial-planning clients what savings account balance would make them feel secure, the silence after that question mark was uncomfortably long. Sometimes, there was no number big enough, despite having emergency funds and insurance policies of every relevant type—potential financial catastrophes neatly underwritten and accounted for.

But it wasn’t just them; when I was able, I hoarded like a prepper. Whether cash for present emergencies, or index funds for Future Maddie, I wanted to reinforce every possible point of failure.

We Americans live in a country with a well-documented lack of social safety nets, with the most vulnerable among us a hair’s breadth from genuine worst-case scenarios.

But that didn’t describe my clients, and it didn’t describe me. Many of us hoard, overplan, and live for the future not because we’re truly vulnerable. We just don’t trust that we can learn how to pick up shattered pieces. In those cases, financial planning past the point of necessity acts as a socially-acceptable pacifier.

Some of my biggest fears have actually come true. Those trials were…different than my anxious former self imagined. The emotional devastation was unfathomable. But the logistics? I was surprised to find that I could, in fact, figure those out as I went.

Who do you call during a middle-of-the-night home hospice emergency? What’s the difference between an informal and a legal separation? How do unemployment benefits work? I now trust myself, with support and self-advocacy skills, to answer previously-unthinkable questions.

Let’s be real: money helps a lot—like, a lot a lot—when excrement hits the proverbial fan. Building an emergency fund and getting the right kinds of insurance are acts of extraordinary self-kindness. Just remember that we have other resources at our disposal, too: professional networks and friendships, degrees from the school of hard knocks, hustle, ingenuity.

Recently, a generous reader emailed me to share the lessons from her own plan-in-flames moment—a series of devastating blows, financial ones included.

“Even if you do lose all of your material wealth and belongings, your life is not over,” she wrote. “You can start again.”

Spoken like someone who trusts herself.

💬 What about you?

I’m curious to know. Do you trust yourself to figure things out when your plans go sideways? Has that trust ever wavered?

Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.

Warmly,
Maddie